Careful What You Bet On Ch. 03

I worked till lunch before heading home to get ready. I was so excited. I couldn't wait to strip Wendy. Ironically, I had only given Wendy my size, 14. Neither of us knew what the other looked like or how far this would go. I quickly logged on and read Jeff's posting before I stepped in the shower to shave again, though the waxing I had done at my local salon looked great.

Jeff was brushing his teeth and grinning at me when I stepped out of the shower. Apparently, my happiness and excitement were visible through the shower doors.

"You could lose, you know."

"I won't. I can't." I said confidently.

"But you want me to help Wendy, if you do lose?"

"Absolutely. Fair is fair. Go as far as you want with her or anyone else. No limits. Ok?"

"Ok, honey." He kissed me on the cheek and whispered "Good luck."

"You want me to lose?"

"Of course not, but I'll be horny as hell if you do."

What did one wear to a strip/wrestling match? I finally settled on navy silk dress pants and a cream cashmere top while Jeff wore black dress pants and a blue shirt, looking stunning as usual in his 6-foot average frame with brown hair and eyes.

At precisely 2:30pm, Jeff and I knocked on the suite door and waited until Wendy promptly opened it and, paying no attention to me, hugged Jeff warmly and pressed herself against him.

I stared at her rubbing against Jeff and looked to Ron who was simply smiling. Jeff appeared caught off guard but did not appear to object to the contact in any way. Just how far would things go this weekend I wondered?

Ron was built similar to Jeff, tall, dark and damn good-looking. "What is it you do?" I asked making small talk.

He smiled and looked at his wife as if sharing an inside secret. "Oh, he's a doctor," said Wendy.

"Yes I am, and I can't tell you how much I am looking forward to this afternoon. Thank you Ashley for agreeing to take my wife on. Not many women challenge her little alone bet her."

"Oh it will be my pleasure to bring her down. You won't mind helping me, umm, expose her will you?"

"Certainly not. But I also won't mind helping her expose you."

"Would you like a drink... Jeff?" asked Wendy playing hostess to my displeasure since this was suppose to be neutral ground and she was obviously getting Jeff to warm up to her.

"A glass of wine would be great," said Jeff noticing Ron drinking the same.

Wendy gracefully went over and poured Jeff a glass and brought it back and sat beside him, handing it to him so he had to touch her hand. I felt so awkward standing at the end of the couch, feeling very out of place in this cozy little gathering.

"So, Jeff, I saw your post just before lunch. Very nice. Do you need help setting up or anything?"

"Thanks anyway Ron but I'm already whenever the ladies are." To emphasize his point he flipped open his laptop and took out his digital camera.

My nerves hit me at Jeff's sentence. The time was here. No getting out of it now.

"Well, just don't be easy on Wendy if she loses. Believe me, she certainly won't be on Ashley."

"We won't," replied Jeff easily liking Ron.

Well, thank heavens for small miracles. Jeff said 'we', meaning he remembered I existed. Why was I starting to doubt myself now?

"You know, part of me hopes to see Ash strip her bare."

"I know, I feel the same way."

"Isn't that horrible?"

"Nope!" said Jeff. "They got themselves into this."

"Very true, they did."

"Any last questions Ashley?" asked Wendy.

"What limits does the winner have?"

"Hmmm, no bestiality, any sex must be safe and no degrading permanent markings, obviously red marks are not forbidden. Does that cover it?"

"Very well. Thank you."

"Who poses first? I assume you want them to be identical to be fair," asked Jeff.

"She can, since I'm not ready," I replied.

Wendy went and stood in front of the coffee table, just feet in front of Jeff and Ron, and smiled at them before turning and smiling directly at me. Never taking her gaze of me, she reached up and slowly undid each button of her white blouse revealing a bright orange skimpy bikini top that tied at her neck, back and between her perfect breasts. Wendy had a flawless figure. Far better than her clothes revealed. She had three kids? Her breasts were quite adequate but not large by any means, her tummy was flat, and skin a golden tan color. Knowing exactly what I was thinking about her body, as only other women can, Wendy smiled wickedly and turned to look at the guys.

"Ready?" she asked.

Both guys were too speechless to say anything at her brazenness and total openness with her perfect body so they merely nodded with lust filled eyes.

Even several feet away, I heard the guys intake of air as they held their breath and watched this beauty unbutton her button and slowly lower the zipper before letting her pants fall easily to her feet revealing a matching skimpy bottom that tied just below each hip bone.

Smiling cruelly, even in the guys eyes, she turned and directly faced me, daring me to look at her perfect body before she finally said in a whiny, impatient, teenage voice, "Your turn."

I took the bag Wendy gave me and turned to go to the bathroom to change as Ron moved the furniture and Jeff prepared to take Wendy's before shots.

"Oh Ash, wait, you'll want to see my before shots so you can pose the same," she called after me.

"Good idea," said Jeff, not catching her double meaning that was not lost of me.

And with that, Wendy turned and went over and opened the big huge picture windows, cascading the room with bright sunlight and waved to the approximately hundred people working in the office building across the street. I couldn't tell how many floors were above them but enough that a lot of people could now see in our room, if they chose too. And who wouldn't, with a scantly clad, 30-something, mother of 3, posing in the window and waving, wearing only a skimpy florescent orange bikini?

Jeff looked shocked but then smiled as he realized just how evil this woman could possibly be and happily snapped the front picture of her with her perfect breasts, flat stomach, tanned body and oh-so sweet looking pussy that was barely covered by the thin material. Then she turned and waved to her audience again; this time allowing Jeff to capture her equally perfect ass barely confined by the material.

Turning and smiling at everyone, Wendy confidently walked over and sat on the end coffee table, waiting for Jeff and Ron to get into position to see this.

She winked at both of them before she turned to me and said, "Now watch closely for the up close and personal shot, Big Tits." And with that she tilted her thighs forward, thrusting all of her pussy up towards the camera. Only a small piece of skin hung against her suit. Damn she was in great shape. Next she leaned forward and placed her hands on her knees and tilted her shoulders back so every inch of her breasts were thrust forward.

"Ron, be a dear and make sure I'm not touching myself."

"Nope, no part of your boobs is touching your body dear."

"Great! I'm ready."

In all Jeff's years of experience, he had never seen a picture so perfect. It showed her confidence, spirit, slight bitchiness but also her pretty face, short stylish dark hair, perfect boobs and perfectly trimmed pussy. He quickly uploaded them and showed her.

"Perfect! Your turn Ashley, Big Tits."

Wendy beamed as I paled ten shades and in front of everyone. Quickly I turned and ran for the bathroom.

Oh my God, I thought. I was a good ten sizes bigger than Wendy was. Though not flabby, I had way more padding then Wendy. I cringed at my body while Wendy loved hers, and with good reason. Sure, Wendy was in control now but I knew that would change cause size and strength were differently with me. Oh how I couldn't wait to take this Bitch down.

I pulled up my bikini bottoms, cringing at my flabby legs, thighs and fat butt as I struggled into the bikini bottom. Luckily, my waxing worked and no hairs were visible I thought thankfully as I tied both sides in place. It certainly was thin material I realized as my dark hairs were noticeable close up, but that was the point wasn't it. My tummy hung an inch or so over the material which caused me great embarrassment but nothing I knew to the embarrassment I would feel when Wendy saw me.

Now as I stood up and reached for the top piece, I couldn't help comparing every blessed inch of my body to Wendy's. Everything was just...well, heavier, fatter. Ugh. I turned the top and tied it securely backwards and then pulled it around so the tie was in the middle of my back. Next, I pulled the cup parts up and tied them in the centre between my mounds. Oh, lord! I forgot my top was two sizes bigger than my bottoms so even though Wendy bought the correct size I asked for, it barely covered my breasts. I knew the style was meant to show skin on both the sides and underneath, but this was almost indecent. Heck, even without breathing I was close to popping.

Resigned, I stretched the two cups as much as I could to cover myself and then tied the two strings behind my neck. As a last thought, I pulled my hair into a pony tail, took a deep breath and headed for the door knowing I had done the best I could and would take comfort in the fact that stripping Wendy bare would make up for this little embarrassment.

I took two steps in to the living room and stopped when I heard Wendy gasp as I was forced to let everyone...well, look at me. Flab everywhere, tits drooping and almost popping, small roll on my tummy, wide cheeks allowing my bottoms to reveal more skin than it covered.

"Wow, Big Tits is right. They're huge." Cheered Wendy as she stepped around me and lifted my arms straight out so she could adequately see.

"Hey! Inspection! She cheated! Her knots are double tied. No far!"

Oh lord, I knew it was true. I forgot that rule. I quickly reached for them when Wendy said, "No way. Let Jeff. You'll cheat again."

Everyone watched Jeff carefully redo all the knots being careful not to expose me, just yet. He retied them as tight as possible but the strings were so silky that they wouldn't hold tight, it would be very easy to undo these with a simple tug, he thought. He now also knew how flimsy the material was. Heck, one hard tug and it would rip so easily. Oh man... This promised to be good.

He looked over at Ron, who obviously also knew how thin the material was and how silky the straps were. Ron smiled and shrugged. Jeff smiled in return, agreeing with his unspoken statement that it was definitely fair since both we wearing the same.

"Ok, her before pictures!" cheered Wendy like it was Christmas. "Make sure she is exactly like I was."

"Ashley. In front of the window please," asked Jeff.

Reluctantly I faced him and placed my arms up spread, exactly like Wendy had done. It was embarrassing to stand like this in front of Jeff, Wendy and Ron. Wendy appeared to be studying my suit in great detail, memorizing the knots. Oh dear.

"Ok, turn around and wave," said Ron.

"Wave?" I choked.

"Yep, she did."

Trying to just get this over as quick as possible, I reached up and waved.

"Oohh, nice cheek. You'll be glad you waxed when you see this picture."

Damn Wendy! As her meaning hit me, I could feel the cold air definitely hitting my cheek. The majority of the material on the left side was definitely in my crack, leaving my bare cheek defenseless and exposed for the camera and Wendy's wisecracks.

"Ok," whispered Jeff. The soft tone of his loving voice helped me more than anything.

"Oohh goody, goody, goody. Now the close up. Let's see those tits hang, Big Tits."

I didn't wait to be told and instead moved voluntarily hoping to get this over with, taking a seat on the end of the coffee table, leaning forward with my hands on my knees.

"Exactly!" snapped Wendy leaning over Jeff's shoulder on the couch to see and giving him a massage in the process.

"Ash, please lean forward," asked Jeff softly. Thank goodness for him being here, I thought even though he was moaning softly as Wendy worked his muscles.

"Good. Now dangle," said Ron.

I adjusted humiliated.

"More," said Ron.

"Please!" I pleaded, with whom I didn't know.

Jeff reached to the edge of the couch and turned the laptop screen to show me Wendy's picture already posted.

"A lot more Ash," said Jeff. "Shoulders forward so they are totally hanging."

"Nope!" she cheered triumphantly. "More! They are still touching her."

Jeff looked and confirmed Wendy's diagnosis. "They are Ash. More."

"But I'll pop!"

"Pop goes Ash's tits," sang Wendy to the tune of Pop Goes the Weasel.

Even Jeff laughed with Ron at her song before he said, "More Ash. Fair is Fair. And need I remind you that you told her to go first and choose the poses. Now dangle! It's almost 3:30."

I slowly moved a bit more utterly embarrassed as I looked down and watched the material slowly let more and more of my breast show. My whole breast was now visible and areas of my light pinkish/brown areola would be seen any minute. I saw Jeff realize this and look up at Ron and Wendy, who both smiled wickedly back. Oh ya, they saw and were enjoying my misery immensely.

"Keep going, Big Tits," said Wendy.

"But I'll pop! Please!"

"Oh well!" cheered Wendy.

I couldn't take it anymore so I closed my eyes knowing the material was definitely heading towards the nipples and letting my areolas come into view quite nicely for my audience.

"And just think, Big Tits, you offered Jeff's services," said a delighted Wendy.

"Uugghh!" I groaned.

"Aren't you glad Jeff?" asked Ron.

"Hell yes!"

"Just a bit more...a bit ... more...there!" cheered Wendy.

I looked down horrified just as Jeff snapped the picture. The material was hairs away from my right nipple, which meant... Oh no, suddenly I had a horrible realization. I knew everyone was watching me but I couldn't help it. I snapped my head to see my left breast, which was far bigger than the right. Sure enough, the edge of the nipple was starting to show very nicely. Jeff snapped again with me looking right at my slightly exposed nipple, horrified.

"Good thing this turns you on Ash or you would have popped before the game even started." Wendy's statement couldn't have been truer, I thought sadly.

Then she continued, " But what a way to give everyone a glimpse of what is about to come. I'll have to remember how huge your left tit is. Surely, I can't miss if I go for it. Oh, and can I clarify that losing your top and bottom in a single match is game, right?"

"Yes."

"And since we're both women, nothing is off limits right as we discussed."

"Right."

Jeff turned the screen to show me my pictures before he posted them.

Still sitting on the coffee table, I leaned forward to look at the screen at the exact same time as Wendy leaned over the arm of the couch and almost into Jeff's lap.

"Oh no!" I cried. "Please retake."

"Let me see," said Wendy as she fell completely into Jeff's lap. I watched shocked as Jeff lifted the laptop up and set it in her lap, which was sitting comfortable in his. "Majority wins. Ron what do you think? I absolutely love them. The view of her cheek is cute but her face-on is priceless. I think it adequately and honestly shows her mammoth tits about to pop, rolls on her tummy flopping over her bottoms and her embarrassment as I watch on."

"Ron, dear?"

"Post."

I watched Jeff hit some buttons and knew instantly the he agreed with them over me as he posted them even before Wendy reached up and kissed his cheek singing "Goody! Goody! Goody!"